Synthesis and styrene copolymerization of novel trisubstituted ethylenes: Chlorophenoxy ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates
Jose L Zepeda, Ricki L Coston, Mayra A Flores, Aaron Graham, Francesco Guzzo, Naquira S Manigault, Ethel S Nieto, Stephan Piven, Sara M Rocus, William S Schjerven, Gregory B Kharas
Novel trisubstituted ethylenes, chlorophenoxy ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2CH(CH3)2(where R is 2-(4-chlorophenoxy), 3-(4-chlorophenoxy), 4-(3-chlorophenoxy), 4-(4-chlorophenoxy), 3-(3,4-dichlorophenoxy), 3-(3,5-dichlorophenoxy), 4-(2,4-dichlorophenoxy) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and isopropyl cyanoacetate, and characterized by CHN analysis, FTIR, 1H and 13C-NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70°C. The compositions of the copolymers were calculated from nitrogen analysis and the structures were analyzed by FTIR, 1H and 13C NMR. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 250-500ºC range with residue (4.9-9.8% wt), which then decomposed in the 500-800ºC range.